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Still sending naked email? Get your protection here

Buckle your seatbelt, encrypt your bits

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Security How-to In this age of brazen, warrantless wiretaps and never-endingdatabreaches, you'd think email encryption would be considered de rigueur. Alas, even among the digerati it's rarely given the time of day because encryption is seen as an exotic undertaking that brings more hassle than benefit.

To be sure, incorporating a robust encryption regimen into a routine that involves sending and receiving hundreds of emails each day won't happen by accident. If you've never done it before, there's a modestly steep learning curve that's necessary not only for you, but for all the people you correspond with. No wonder few people bother.

Jon Callas, CTO of encryption software provider PGP, likens encrypting email to wearing a seatbelt, which a few decades ago was so unpopular that many people only did when they were required by law to do so.

"You only need to wear a seatbelt on the day you get in a crash and you only need to encrypt the one email that's going to get lost," he says. "The way that you make sure you encrypt that one mail that needs to be encrypted is the same way you make sure you wear your seatbelt on the one day you get in a crash and that is you do it all the time."

Your writer was forced to confront his own encryption apathy about a year ago, when asked for a public key by a source promising a juicy scoop. Two days later, the key was proffered, but the experience made it clear that the road to encryption Nirvana - at least for us Windows users - is paved with solutions that are confusing, incomplete, or impractical.

For those so inclined, PGP sells products such as PGP Desktop Email that Callas says "literally passes the my-75-year-old-mother-can-use" test. Your writer, on the other hand, opted for Gpg4Win, a free Windows implementation of the open source Gnu Privacy Guard (GnuPG). Used with the Enigmail add-on for Mozilla's Thunderbird email client, it offers everything needed to generate, store, and manage digital keys for email encryption.

What follows is a step-by-step tutorial for Windows users. (Linux geeks looking for help should seek out Brenno de Winter's excellent how-to here.)